Do offshore betting sites send any tax forms? I've been using [redacted site] for years and never received anything, but also never reported any of it. Now I'm worried...

Offshore betting sites typically don't issue tax forms or report to the IRS since they're operating outside US jurisdiction. However, that doesn't exempt you from the obligation to report your gambling winnings - all gambling income is technically taxable regardless of where it comes from. The lack of reporting from offshore sites creates a documentation gap that puts the burden entirely on you to track and report accurately. If you've had significant winnings, you might want to get your past reporting in order. The IRS has been increasingly focused on unreported gambling income, especially with cryptocurrency transactions sometimes being used for offshore gambling.

The tax code distinguishes between investments and gambling based on the nature of the activity. Business investments are considered productive economic activities, while gambling is viewed as recreational. That said, if you can document that your gambling activities constitute a trade or business (extremely difficult to prove - requires regular, full-time activity with a profit motive), you might be able to deduct losses on Schedule C instead of Schedule A. But for the vast majority of people who gamble occasionally, the IRS will only allow losses to offset wins when itemizing.

Is Form 1096 still required if you e-file the 1099s? I thought it was only for paper filing.

You're absolutely right - Form 1096 is only required if you're paper filing your 1099s. If you e-file directly with the IRS, you don't need to submit a 1096. E-filing is actually required if you have more than 10 forms, and it's generally easier anyway. But for a small startup with just a few contractors, either method works.

This is great advice. I'd also recommend keeping a spreadsheet tracking all contractor payments throughout the year. Makes it way easier when January rolls around and you need to figure out who exceeded the $600 threshold.

Can you really claim home office if you're just making jewelry at your dining table? I thought you needed a dedicated room that's ONLY for business?

You're right that the rules for home office deduction are strict. You need a space used "regularly and exclusively" for business, so a dining table that's also used for family meals wouldn't qualify. However, if you have a dedicated corner of a room with a desk that's only used for your business activities (taking product photos, listing items, managing orders, etc.), that specific area might qualify. You'd calculate the percentage of your home's square footage that this space represents. Many people miss out on this deduction because they think they need an entire separate room, but even a dedicated portion of a room can sometimes qualify.

Same thing happened to me!! My HR department "updated their system" and somehow my withholding got set way too low. I didn't notice on my paychecks because I got a raise at the same time so the take-home amount seemed fine. Definitely check your pay stubs against last year!

21 Is there a minimum dollar threshold where the IRS doesn't really care? Like would they really make a big deal about a $9,800 repair vs. improvement on a rental property tax return? Seems like they'd be more concerned with bigger issues.

19 There's no specific dollar threshold where the IRS "doesn't care" - the rules apply regardless of amount. However, in practical terms, larger amounts are more likely to trigger scrutiny. The real issue isn't about the dollar amount but about following proper tax treatment. Even relatively small incorrect classifications, if discovered during an audit, can lead to adjustments, interest, and potentially penalties. More importantly, they could cause the IRS to expand the scope of their audit to look for other issues, which nobody wants.

24 This is a really good point! Insurance reimbursements can totally change how you report these expenses. Did you have to adjust your deduction based on the insurance payment?

Thanks for this suggestion! Would the IRS consider my taxes "paid on time" if I cancel the direct debit and then use Direct Pay on April 15th instead? I don't want to trigger any late payment penalties.

Yes, as long as you complete the Direct Pay transaction by midnight on April 15th, the IRS considers your payment made on time. The confirmation page you receive serves as proof of timely payment. Just make sure to select "2024" for the tax year and "1040 series" for the reason for payment when you use Direct Pay. Also, keep a copy of your payment confirmation number in case there are any questions later.

That's odd, in my experience the IRS is actually very precise with their direct debit dates. They took mine exactly on the date I specified. Maybe it was your bank that caused the delay?